EP3902847A1 - Procédé de production de fluoropolymères à l'aide de tensioactifs 2-alcoxyacétate - Google Patents

Procédé de production de fluoropolymères à l'aide de tensioactifs 2-alcoxyacétate

Info

Publication number
EP3902847A1
EP3902847A1 EP19906053.4A EP19906053A EP3902847A1 EP 3902847 A1 EP3902847 A1 EP 3902847A1 EP 19906053 A EP19906053 A EP 19906053A EP 3902847 A1 EP3902847 A1 EP 3902847A1
Authority
EP
European Patent Office
Prior art keywords
ppm
reactor
surfactant
initiator
polymerization
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP19906053.4A
Other languages
German (de)
English (en)
Other versions
EP3902847A4 (fr
Inventor
Bhuvanesh Gupta
Bishwajit Santosh BHATTACHARYA
Rajeev Chauhan
Jitendra Kumar RATHOUR
Gaurav Kumar
Chetna Verma
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Gujarat Fluorochemicals Ltd
Indian Institute of Technology Delhi
Original Assignee
Gujarat Fluorochemicals Ltd
Indian Institute of Technology Delhi
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Gujarat Fluorochemicals Ltd, Indian Institute of Technology Delhi filed Critical Gujarat Fluorochemicals Ltd
Publication of EP3902847A1 publication Critical patent/EP3902847A1/fr
Publication of EP3902847A4 publication Critical patent/EP3902847A4/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F14/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
    • C08F14/18—Monomers containing fluorine
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/12—Polymerisation in non-solvents
    • C08F2/16—Aqueous medium
    • C08F2/22—Emulsion polymerisation
    • C08F2/24—Emulsion polymerisation with the aid of emulsifying agents
    • C08F2/26—Emulsion polymerisation with the aid of emulsifying agents anionic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F114/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
    • C08F114/18—Monomers containing fluorine
    • C08F114/24—Trifluorochloroethene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F4/00—Polymerisation catalysts
    • C08F4/28—Oxygen or compounds releasing free oxygen
    • C08F4/32—Organic compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F4/00—Polymerisation catalysts
    • C08F4/28—Oxygen or compounds releasing free oxygen
    • C08F4/32—Organic compounds
    • C08F4/34—Per-compounds with one peroxy-radical

Definitions

  • the present invention pertains to a process for polymerizing fluoromonomers using non-fluorinated surfactants. More particularly, the present invention relates to a process for aqueous polymerization using 2-Alkoxy acetate surfactants.
  • Fluoropolymers attract a lot of attention due to their extreme chemical resistance and favorable dielectric properties. They are generally synthesized from alkenes in which one or more hydrogen atoms have been replaced by fluorine atom.
  • the most important members of this class of polymers are polytetrafluoroethylene (PTFE), aqueous PTFE, fine particle PTFE, polychlorotrifluoroethylene (PCTFE), polyvinyl fluoride (PVF), fluorinated ethylene polymer (FEP), perfluoroalkoxy polymer (PFA) and polyvinylidene fluoride (PVDF). They are primarily manufactured via heterogeneous polymerization reactions including aqueous systems.
  • the reaction requires a monomer and a radical initiator in a suitable aqueous reaction medium.
  • Aqueous polymerization of fluorine containing monomers generally requires a surfactant capable of emulsifying both the reactants and the reaction products for the duration of the polymerization reaction.
  • the surfactant of choice in the synthesis of fluoropolymers is generally a perfluoro surfactant or a partially fluorinated surfactant.
  • the most frequently used perfluoroalkyl surfactant in the production of fluoropolymers is ammonium perfluorooctanoate (AFPO).
  • AFPO ammonium perfluorooctanoate
  • US 7932333 B2 discloses a process comprising polymerizing at least one fluorinated monomer in an aqueous medium containing initiator and polymerization agent to form an aqueous dispersion of particles of fluoropolymer, the polymerization agent comprising fluoropolyether acid or salt thereof having a number average molecular weight of at least about 800 g/mol; and fluoropolyether acid or salt surfactant.
  • United States patent No. US 7777075 B2 provides a fluoroether carboxylic acid which is represented by the general formula (I): Rf 1 0CHFCF20Rf 2 C00M.
  • the fluoroether carboxylic acid can be suitably used as a surfactant.
  • the patent also discloses a method of fluoropolymer production and an aqueous fluoropolymer dispersion, using the fluoroether carboxylic acid as a surfactant.
  • United States Patent No. US 7897682 B2 discloses a process for polymerizing at least one fluorinated monomer in an aqueous medium in the presence of initiator and polymerization agent to form an aqueous dispersion of particles of fluoropolymer having a fluoropolymer solids content of at least about 10% by weight.
  • the polymerization agent is a combination of fluoropolyether acid or salt thereof and hydrocarbon surfactant.
  • PFOS Perfluorooctane sulfonate
  • PFAS polyfluoroalkyl substances
  • current criteria for PFAS are typically in the form of guidance or advisory levels. According to the advisory, any substance may not contain PFOS above the limit of 0.001 % by weight, EU 757/2010. In the U.S., PFOS manufacturing was voluntarily phased out in 2002.
  • a process for the polymerization of fluoromonomers, which uses a nonfluorinated surfactant would solve the aforestated issues of persistence in the eco-system and bio-accumulation of fluorosurfactants, and would lead to cheaper and simplified processes. Consequently, there is a need to explore the use of non-fluorinated surfactants in the aqueous polymerization of fluoromonomers.
  • the main objective of the invention is to overcome the aforestated problems in the prior art.
  • the other objective of the present invention is to provide a process for the aqueous polymerization of fluoromonomers using non-fluorinated surfactants.
  • Yet another objective of the present invention is to provide a process for the aqueous polymerization of fluoropolymers using non-fluorinated 2-Alkoxy acetate surfactants.
  • the present invention relates to a process for aqueous polymerization of fluoromonomers using non-fluorinated surfactants, particularly 2-Alkoxy acetate surfactants.
  • a process for preparing a fluoropolymer in an aqueous medium by a polymerization reaction comprising the steps of:
  • step (a) comprises the steps of:
  • step (b) comprises adding the initiator in one shot into the reactor.
  • the 2-Alkoxy acetate surfactant has a structure of R-O-CH3-COOM, wherein R is a hydrocarbon group, and M is a monovalent cation selected from the group consisting of hydrogen ions, alkali metal ions, and ammonium ions.
  • R is an alkyl group containing 6 to 21 carbon atoms.
  • M is preferably selected from the group consisting of potassium, sodium and ammonium.
  • 2-Alkoxy acetate surfactant is either a compound of formula 1 or formula 2.
  • the aqueous emulsion comprises an initiator, for initiating the polymerization reaction, the initiator being selected from the group consisting of Ammonium Persulphate (APS), Disuccinic Acid Peroxide (DSAP) and combinations thereof.
  • the aqueous emulsion of the present invention may optionally comprise stabilizing agents such as paraffin wax.
  • the reaction temperature is in the range of 20 to 160 ° C, preferably 60 to 130 ° C, and more preferably 75 to 95 ° C.
  • the reaction pressure ranges from 2 to 200 bar.
  • the pressure in the reaction vessel or reactor is 24 bar.
  • reaction mixture is agitated at 50 rpm.
  • the concentration of the surfactant in the reaction mixture ranges from 1000 to 7,000 ppm, and preferably 3000 to 4000 ppm, based on the weight of the aqueous dispersion.
  • the concentration of the initiator ranges from 50 to 2000 ppm, preferably from 50 to 400 ppm and more preferably from 150 to 400 ppm, based on the weight of the aqueous dispersion.
  • the solid content of the fluoropolymer, obtained by the polymerization reaction ranges from 15 to 25% and more preferably from 18 to 25%.
  • the particle size of the fluoropolymer obtained by the polymerization reaction ranges from 180 nm to 240 nm.
  • the polymerization reaction time ranges from 60 to 160 minutes.
  • the fluoromonomer is selected from the group consisting of tetrafluoroethylene, chlorotrifluoroethylene, vinyl fluoride, vinylidene fluoride, hexafluoropropylene, perfluoropropylvinylether, perfluorobutylethylene and combinations thereof.
  • Figure 1 is a flowchart of the process of polymerization of the present invention.
  • the present invention relates to a process for preparing a fluoropolymer in an aqueous medium, comprising:
  • surfactant means a type of molecule which has both hydrophobic and hydrophilic, portions, which allows it to stabilize and disperse hydrophobic molecules and aggregates of hydrophobic molecules in aqueous systems.
  • a preferred group of surfactants for fluoropolymer synthesis according to the embodiments of the present invention includes non- fluorinated carboxylate surfactants, more preferably 2-Alkoxy acetate surfactants.
  • the 2-Alkoxy acetate surfactant has a structure of R-O-CH3- COOM, wherein R is a hydrocarbon group, M is a monovalent cation selected from the group consisting of hydrogen ions, alkali metal ions, and ammonium ions.
  • R is an alkyl group containing 6 to 21 carbon atoms.
  • M can be potassium, sodium or ammonium.
  • the 2-alkoxy acetate surfactant is represented by the formula 1 .
  • Compound of formula 1 is also known by the chemical name- Sodium-2-[(2-hexyldecyl)oxy] acetate.
  • the 2-alkoxy acetate surfactant is represented by the formula 2.
  • Compound of formula 2 is also known by the chemical name Sodium-2-dodecylacetate.
  • fluoromonomer or the expression“fluorinated monomer” means a polymerizable alkene which contains at least one fluorine atom, fluoroalkyl group, or fluoroalkoxy group attached to the double bond of the alkene that undergoes polymerization.
  • fluoropolymer means a polymer formed by the polymerization of at least one fluoromonomer, and it is inclusive of homopolymers, copolymers, terpolymers and higher polymers.
  • fluoromonomers include, without limitation, vinyl fluoride, vinylidine fluoride (VDF), 1 -fluoro-1 -chloro-ethylene, perfluoropropylvinylether, trifluoroethylene (TrFE), tetrafluoroethylene (TFE), hexafluoropropene (HFP), chlorotrifluoroethylene (CTFE), 1 -chloro-2,2-difluoroethylene, perfluoromethyl vinylether (PMVE), etc.
  • the fluoromonomer is tetrafluoroethylene (TFE) and the fluoropolymer obtained as a result of the polymerization reaction is polytetrafluoroethylene (PTFE).
  • the aqueous emulsion comprises an initiator for initiating the polymerization process.
  • initiator and the expressions“radical initiator” and “free radical initiator” refer to a chemical that is capable of providing a source of free radicals, either induced spontaneously, or by exposure to heat or light. Examples of suitable initiators include peroxides, peroxydicarbonates and azo compounds. “Initiators” also includes redox systems useful in providing a source of free radicals.
  • the term“radical” and the expression“free radical” refer to a chemical species that contains at least one unpaired electron.
  • the radical initiator is added to the reaction mixture in an amount sufficient to initiate and maintain the polymerization reaction rate. Preferably, the addition of the initiator into the reaction vessel or reactor is carried out in one shot.
  • the radical initiator may comprise a persulfate salt, such as sodium persulfate, potassium persulfate, or ammonium persulfate.
  • the radical initiator may comprise a redox system.“Redox system” is understood by a person skilled in the art to mean a system comprising an oxidizing agent, a reducing agent and optionally, a promoter as an electron transfer medium.
  • the radical initiator is either Disuccinic Acid Peroxide (DSAP), Ammonium Persulphate (APS), Potassium Persulfate (KPS) or combinations thereof.
  • the process parameters for carrying out the polymerization of the fluoromonomers in accordance with the present invention, illustrated in Figure 1 , 100, are as follows.
  • the temperature used for polymerization may vary, for example, from 20 to 160°C, depending on the initiator system chosen and the reactivity of the fluoromonomer (s) selected.
  • the polymerization is carried out at a temperature in the range from 60 to 130 °C, and more preferably, in a range of 75 to 95 ° C.
  • the pressure used for polymerization may vary from 2-200 bar, depending on the reaction equipment, the initiator system, and the monomer selection. In a preferred embodiment the reaction is carried out at a pressure of 24 bar.
  • the polymerization occurs under stirring or agitation.
  • the stirring may be constant, or may be varied to optimize process conditions during the course of the polymerization. In one embodiment, both multiple stirring speeds and multiple temperatures are used for controlling the reaction.
  • a pressurized polymerization reactor equipped with a stirrer and heat control means is charged with water, preferably deionized water, non-fluorinated 2-Alkoxy acetate surfactant in accordance with the invention and at least one fluoromonomer.
  • the surfactant content ranges from 1000 ppm to 7000 ppm and preferably from 3000 to 4000 ppm, based on the weight of aqueous dispersion. In a preferred embodiment, the surfactant content is 3125 ppm, based on the weight of the aqueous fluoropolymer dispersion.
  • the surfactant is added in one shot into the reaction vessel.
  • the mixture may optionally contain paraffin wax.
  • the reactor is then heated up to the reaction temperature, and the pressure is increased by adding fluoromonomer.
  • initiators are added into the reaction vessel to initiate the polymerization reaction in step 1 10.
  • the initiator is introduced into the reaction vessel in one shot.
  • the initiator concentration ranges from 50 to 2000 ppm and preferably from 50 to 400 ppm. In a preferred embodiment, the initiator concentration ranges from 150 to 400 ppm, based on the weight of the aqueous dispersion.
  • air Prior to introduction of the surfactant and monomer or monomers into the reaction vessel, air is preferably removed from the reactor in order to obtain an oxygen-free environment for the polymerization reaction.
  • the oxygen is removed from the reaction vessel until its concentration is less than 10 ppm.
  • the reactor may also be purged with a neutral gas such as, for example, nitrogen or argon.
  • the reactor Upon completion of the polymerization reaction, the reactor is brought to ambient temperature and the residual unreacted monomer is vented to atmospheric pressure.
  • the aqueous reaction medium containing the fluoropolymer is then recovered from the reaction vessel.
  • the solid content ranges from 15 to 25 %, and more preferably from 18 to 25%.
  • the particle size of the fluoropolymer particles ranges from 180 nm to 240 nm.
  • the polymerization process was carried out in a 150 L horizontal reactor, with six blade agitator. 96 L of de-ionized water, and 4 kg of paraffin wax were added into the reactor. Oxygen was removed from the reactor until its concentration was less than 10 ppm. After that, the surfactant, molecule of formula 1 , also known as Sodium 2-[(2-hexyldecyl)oxy] acetate, 3125 ppm , was added in one shot into the reactor. Thereafter, the addition of Tetrafluoroethylene (TFE) resulted in an increase in the pressure to 24 bar and the temperature was increased to 80 to 95 °C.
  • TFE Tetrafluoroethylene
  • APS Ammonium Persulphate
  • the reactor is brought to ambient temperature and the residual unreacted monomer is vented to atmospheric pressure.
  • the aqueous reaction medium containing the fluoropolymer is then recovered from the reaction vessel.
  • Examples 2 to 5 were also carried out in an identical manner and the ingredients and reaction parameters of Examples 1 to 5 are illustrated in Table 1 below.
  • the latex particle size of the polymer was determined by -Dynamic Laser light scattering for analysis of particle size using a Nano particle Analyzer - HORIBA SZ-100.
  • example 1 pertains to the polymerization of tetrafluoroethylene
  • the process may be applied to any monomer selected from the group consisting of tetrafluoroethylene, chlorotrifluoroethylene, vinyl fluoride, vinylidene fluoride, hexafluoropropylene, perfluoropropylvinylether, perfluorobutylethylene and combinations thereof. All parameters were derived in accordance with ASTM
  • the polymerization process was carried out in a 150 L reactor. 96 L of de ionized water, and 4 kg of paraffin wax were added into the reactor. Oxygen was removed from the reactor until its concentration was less than 10 ppm. After that, the surfactant, molecule of formula 2, also known as Sodium Salt of 2-dodecyloxyacetic acid (Sodium-2-dodecyloxyacetate), 3125 ppm, was added in one shot into the reactor. Thereafter, the addition of Tetrafluoroethylene (TFE) resulted in an increase in the pressure to 24 bar and the temperature was increased to 80 to 95 °C.
  • TFE Tetrafluoroethylene
  • a solution comprising an initiator, Disuccinic Acid Peroxide (DSAP), was added so that the final concentration of initiator in the reaction mixture was 156 ppm.
  • DSAP Disuccinic Acid Peroxide
  • the reactor is brought to ambient temperature and the residual unreacted monomer is vented to atmospheric pressure.
  • the aqueous reaction medium containing the fluoropolymer is then recovered from the reaction vessel.
  • Examples 7 to 9 were also carried out in an identical manner and the ingredients and reaction parameters of Examples 6 to 9 are illustrated in Table 2 below.
  • example 6 pertains to the polymerization of tetrafluoroethylene
  • the process may be applied to any monomer selected from the group consisting of tetrafluoroethylene, chlorotrifluoroethylene, vinyl fluoride, vinylidene fluoride, hexafluoropropylene, perfluoropropylvinylether, perfluorobutylethylene and combinations thereof.
  • the polymerization process was carried out in a 150 L reactor. 83 L of de ionized water with 160 PPM of sodium pyro-phosphate as a buffer is added to the reactor. Oxygen was removed from the reactor until its concentration was less than 10 ppm. After that, the surfactant, molecule of formula 1 , also known as Sodium Salt of 2-dodecyloxyacetic acid (Sodium-2- dodecyloxyacetate), 4200 ppm, was added in one shot into the reactor.
  • the surfactant molecule of formula 1 , also known as Sodium Salt of 2-dodecyloxyacetic acid (Sodium-2- dodecyloxyacetate), 4200 ppm
  • TFE Tetrafluoroethylene
  • HFP Hexafluoropropylene
  • PPVE perfluoropropylvinyl ether
  • the reactor Upon completion of the polymerization reaction after metering of 27.1 kg TFE and 2.4 kg FIFP in 400 minutes, the reactor is brought to ambient temperature and the residual unreacted monomer is vented to atmospheric pressure.
  • the resulting polymer latex had a solid content of 27% by weight with a primary particle size of 234.2 nm.
  • the latex particle size of the polymer was determined by -Dynamic Laser light scattering for analysis of particle size using a Nano particle Analyzer - HORIBA SZ-100.
  • the resulting polymer powder after coagulation had the following properties: MFR (Melt Flow Rate): 26 g/10 min (372 °C; 5 kg load); Melting Temperature: 280.6 °C; Enthalpy: 27.6 J/g. All properties were derived in accordance with ASTM D 21 16.
  • the polymerization process was carried out in a 150 L reactor. 77 L of de ionized water with 135 PPM of sodium pyro-phosphate as a buffer is added to the reactor. Oxygen was removed from the reactor until its concentration was less than 10 ppm. After that, the surfactant, molecule of formula 1 , also known as Sodium Salt of 2-dodecyloxyacetic acid (Sodium-2- dodecyloxyacetate), 4500 ppm, was added in one shot into the reactor. Thereafter, the addition of 1 .3 kg Tetrafluoroethylene (TFE) and 5.0 kg Flexafluoropropylene (HFP) resulted in an increase in the pressure to 22 bar and the temperature was increased to 94 °C.
  • TFE Tetrafluoroethylene
  • HFP Flexafluoropropylene
  • a solution comprising initiators Potassium persulfate and ammonium persulfate (1 % solution), was added at a starting rate of 15 ml/min, and gradually reduced to 9 ml/min. 59 PPM ethane gas was added as chain transfer agent after the reaction kicks off as indicated by a pressure drop of 0.5 bar.
  • the reactor was brought to ambient temperature and the residual unreacted monomer was vented to atmospheric pressure.
  • the resulting polymer latex had a solid content of 29% by weight with a primary particle size of 235.2 nm.
  • the latex particle size of the polymer was determined by -Dynamic Laser light scattering for analysis of particle size using a Nano particle Analyzer - HORIBA SZ-100.
  • the resulting polymer powder after coagulation had the following properties: MFR: 24 g/10 min (372 °C; 5 kg load); Melting Temperature: 284.3 °C; Enthalpy: 24.1 J/g. All properties were derived in accordance with ASTM D 21 16.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Polymerisation Methods In General (AREA)

Abstract

La présente invention concerne un procédé de polymérisation de monomères fluorés dans un milieu aqueux, ledit procédé comprenant les étapes consistant à: former une émulsion aqueuse comprenant un tensioactif 2-alcoxyacétate et un monomère fluoré dans un réacteur; et déclencher la polymérisation dudit monomère fluoré par ajout d'un initiateur dans le mélange de réaction. De préférence, le tensioactif utilisé dans le présent procédé est soit le sodium 2-[(2-hexyldécyl)oxy] acétate ou le sodium 2-dodécyloxyacétate.
EP19906053.4A 2018-12-24 2019-12-23 Procédé de production de fluoropolymères à l'aide de tensioactifs 2-alcoxyacétate Withdrawn EP3902847A4 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
IN201811048944 2018-12-24
IN201911003128 2019-01-25
PCT/IN2019/050952 WO2020136679A1 (fr) 2018-12-24 2019-12-23 Procédé de production de fluoropolymères à l'aide de tensioactifs 2-alcoxyacétate

Publications (2)

Publication Number Publication Date
EP3902847A1 true EP3902847A1 (fr) 2021-11-03
EP3902847A4 EP3902847A4 (fr) 2022-11-02

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Application Number Title Priority Date Filing Date
EP19906053.4A Withdrawn EP3902847A4 (fr) 2018-12-24 2019-12-23 Procédé de production de fluoropolymères à l'aide de tensioactifs 2-alcoxyacétate

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Country Link
US (1) US20220081494A1 (fr)
EP (1) EP3902847A4 (fr)
KR (1) KR20210118835A (fr)
CN (1) CN113490694A (fr)
BR (1) BR112021012397A2 (fr)
GB (1) GB2598663B (fr)
WO (1) WO2020136679A1 (fr)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA3151436A1 (fr) * 2019-10-11 2021-04-15 Rajeev Chauhan Procede de preparation de polymeres fluores et d'elastomeres fluores en presence d'un tensioactif contenant un hydrocarbure de type sulfonate non fluore de celui-ci

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6869997B2 (en) * 2003-05-06 2005-03-22 Arkema, Inc. Polymerization of fluoromonomers using a 3-allyloxy-2-hydroxy-1-propanesulfonic acid salt as surfactant
WO2008019155A1 (fr) * 2006-08-11 2008-02-14 The University Of North Carolina At Chapel Hill Procédé de polymérisation de fluoromonomère
EP3514185A1 (fr) * 2010-09-01 2019-07-24 Arkema, Inc. Procédé de fabrication de polymères fluorés à l'aide de monomères fonctionnalisés par acide

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GB202110573D0 (en) 2021-09-08
GB2598663B (en) 2022-09-07
EP3902847A4 (fr) 2022-11-02
GB2598663A (en) 2022-03-09
WO2020136679A1 (fr) 2020-07-02
KR20210118835A (ko) 2021-10-01
BR112021012397A2 (pt) 2021-09-08
US20220081494A1 (en) 2022-03-17
CN113490694A (zh) 2021-10-08

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